FIELD OF THE INVENTION
This invention is directed to new organic compounds and is particularly concerned with 1,2-dioxo-as-tri-azinobenzodiazepines of formula V, intermediates thereto of formula II, and the process therefor.
The novel compounds and the processes of production therefor can be illustratively represented as follows:
Method A: ##STR4##
Method B: ##STR5## wherein R" is alkyl of 1 to 3 carbon atoms, inclusive, ##STR6## in which n is 2 or 3 and X is hydrogen, fluoro or chloro; and R.sub.4 and R.sub.5 are alkyl of 1 or 2 carbon atoms, or together are the group ##STR7## wherein R.sub.2 is hydrogen, methyl or ethyl; wherein R.sub.3 is hydrogen, fluoro, chloro, bromo, nitro or trifluoromethyl; wherein Ar is phenyl, o-chlorophenyl, o-fluorophenyl, 2,6-difluorophenyl or 2-pyridyl.
When the compound I VA R" is ##STR8## (as above defined) the compound is submitted additionally to acid hydrolysis to give compound I VB: ##STR9## in which X, n, R.sub.2, R.sub.3 and Ar are defined as above.
The process of Method A of this invention comprises: treating a compound of formula I with an alkyl oxalyl chloride in the presence of a base at between 0.degree. and -80.degree. C. to obtain a compound of formula II; cyclizing compound II by heating it (preferably with a base) to obtain compound III compound III corresponds to compound V in which R.sub.1 is hydrogen!.
When a compound of formula V is desired in which R.sub.1 is other than hydrogen, compound III can be alkylated in a conventional manner, e.g., with an alkyl halide and sodium hydride or another strong base to give compound I VA above, and if compound I VA is a ketal, it is additionally hydrolized to give compound I VB.
The process of Method B consists in treating a 2-thio-benzodiazepine of the formula i with ethyl oxalylhydrazide to give the intermediate of formula II which can be cyclized by heating to a compound of formula III.
The invention claims the compounds of formulae V, the intermediates of formula II, and the pharmacologically acceptable acid addition salts thereof, and the process to make these compounds.